#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003662.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2003662 loop_ _publ_author_name 'Baradarani, M. M.' 'Beddoes, R. L.' 'Mills, O. S.' 'Joule, J. A.' _publ_section_title ; A Naphthalene-Fused Tricyclic Orthoamide ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1345 _journal_page_last 1347 _journal_paper_doi 10.1107/S010827019401471X _journal_volume 51 _journal_year 1995 _chemical_compound_source 'recrystallization from methanol' _chemical_formula_moiety 'C17 H19 N3' _chemical_formula_sum 'C17 H19 N3' _chemical_formula_weight 265.34 _space_group_IT_number 5 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 1 2 1' _atom_type_scat_source 'IntTabIV; Cromer & Waber (1974)' _cell_angle_alpha 90 _cell_angle_beta 136.53(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 25.166(1) _cell_length_b 8.588(1) _cell_length_c 18.382(1) _cell_measurement_reflns_used 100 _cell_measurement_temperature 296.0(10) _cell_measurement_theta_max 12.8 _cell_measurement_theta_min 7.6 _cell_volume 2733(2) _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.04 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 2664 _diffrn_reflns_theta_max 25 _diffrn_standards_decay_% insignificant _diffrn_standards_interval_count 150 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu 0.13 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.29 _exptl_crystal_description prismatic _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.5 _refine_diff_density_min -0.5 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.12 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 361 _refine_ls_number_reflns 1901 _refine_ls_R_factor_obs 0.032 _refine_ls_shift/esd_max 0.9 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'weights: empirical parabolic, w = 1/(0.62-0.024F+0.008F^2^)^1/2^' _refine_ls_wR_factor_obs 0.041 _reflns_number_observed 1901 _reflns_number_total 2205 _reflns_observed_criterion >3\s(F) _cod_data_source_file ha1136.cif _cod_data_source_block ha1136a _cod_depositor_comments ; The following automatic conversions were performed: '_cell_measurement_temperature' value '296+-1' was changed to '296.0(10)' - precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_cell_measurement_temperature' value '296+-1' was changed to '296.0(10)' - precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2733.2 _cod_original_sg_symbol_H-M 'C 2' _cod_database_code 2003662 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,-z 1/2+x,1/2+y,z 1/2-x,1/2+y,-z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv C1 .3084(2) .4150 -.0395(2) 3.9(3) N2 .2987(1) .5527(4) -.0044(2) 3.9(3) C3 .2686(2) .6816(5) -.0789(3) 4.7(4) C4 .3260(2) .7194(5) -.0821(3) 4.6(3) C5 .3412(2) .5736(5) -.1115(3) 4.6(4) N6 .3652(2) .4419(4) -.0414(2) 3.9(3) C7 .3705(2) .3030(5) -.0827(3) 5.3(4) C8 .3872(3) .1563(5) -.0222(3) 6.1(5) C9 .3286(3) .1420(5) -.0203(3) 5.6(5) N10 .3294(2) .2830(4) .0249(2) 4.2(3) C11 .3917(2) .3046(5) .1349(3) 3.8(3) C12 .4379(2) .1848(5) .2040(3) 5.0(4) C13 .4968(2) .2129(6) .3143(3) 5.3(4) C14 .5085(2) .3560(6) .3535(3) 5.0(4) C15 .4614(2) .4825(5) .2848(3) 4.2(3) C16 .4706(2) .6325(6) .3230(3) 5.2(3) C17 .4246(2) .7511(5) .2551(3) 5.4(5) C18 .3678(2) .7284(5) .1452(3) 4.6(3) C19 .3565(2) .5841(5) .1037(2) 3.7(3) C20 .4027(2) .4565(5) .1736(2) 3.6(3) C21 .1607(2) .2598(5) .3420(3) 4.1(2) N22 .2080(2) .3913(4) .3702(2) 4.5(2) C23 .1619(3) .5328(5) .3243(4) 5.7(5) C24 .0981(3) .5191(5) .2050(4) 6.2(5) C25 .0512(2) .3746(5) .1732(3) 5.5(4) N26 .0998(2) .2346(4) .2271(2) 3.9(2) C27 .0502(2) .1036(5) .1991(3) 4.6(3) C28 .0961(2) -.0417(5) .2602(3) 4.7(3) C29 .1583(2) -.0050(5) .3780(3) 5.2(4) N30 .2072(2) .1226(4) .3992(2) 4.3(3) C31 .2624(2) .0902(5) .4006(2) 4.0(2) C32 .2943(2) -.0545(5) .4226(3) 5.4(3) C33 .3512(2) -.0775(6) .4260(3) 6.5(5) C34 .3754(2) .0373(6) .4058(3) 6.1(5) C35 .3447(2) .1887(5) .3834(3) 4.9(3) C36 .3686(2) .3145(7) .3625(3) 5.9(4) C37 .3395(2) .4580(6) .3444(3) 6.0(5) C38 .2848(2) .4879(5) .3444(3) 5.2(4) C39 .2594(2) .3680(5) .3632(2) 4.1(2) C40 .2881(2) .2165(5) .3814(2) 4.0(2) H1 .259 .392 -.112 ? H31 .261 .772 -.056 ? H32 .219 .649 -.150 ? H41 .375 .755 -.012 ? H42 .305 .799 -.135 ? H51 .382 .594 -.106 ? H52 .294 .544 -.185 ? H71 .412 .317 -.077 ? H72 .321 .288 -.157 ? H81 .439 .162 .051 ? H82 .384 .063 -.057 ? H91 .341 .050 .023 ? H92 .277 .127 -.093 ? H12 .430 .078 .177 ? H13 .530 .125 .363 ? H14 .550 .372 .430 ? H16 .511 .650 .399 ? H17 .431 .853 .283 ? H18 .336 .815 .098 ? H201 .135 .286 .363 ? H231 .195 .623 .345 ? H232 .139 .549 .350 ? H241 .121 .514 .179 ? H242 .065 .612 .175 ? H251 .014 .362 .097 ? H252 .023 .390 .191 ? H271 .014 .083 .123 ? H272 .021 .134 .214 ? H281 .120 -.077 .239 ? H282 .062 -.121 .245 ? H291 .190 -.097 .418 ? H292 .134 .028 .400 ? H321 .277 -.141 .436 ? H331 .374 -.180 .444 ? H341 .414 .018 .406 ? H361 .406 .299 .361 ? H371 .357 .545 .331 ? H381 .264 .595 .331 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 N2 C3 109.9(2) yes C1 N2 C19 116.9(2) yes C3 N2 C19 119.0(3) yes C1 N6 C5 110.4(2) yes C1 N6 C7 110.1(2) yes C5 N6 C7 107.9(2) yes C1 N10 C9 110.3(2) yes C1 N10 C11 115.9(3) yes C9 N10 C11 117.9(3) yes C21 N22 C23 110.0(3) yes C21 N22 C39 115.6(3) yes C23 N22 C39 118.1(3) yes C21 N26 C25 109.7(3) yes C21 N26 C27 110.5(2) yes C25 N26 C27 108.3(2) yes C21 N30 C29 109.7(2) yes C21 N30 C31 116.3(3) yes C29 N30 C31 119.0(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N2 C1 1.450(5) yes N2 C3 1.473(6) yes N2 C19 1.395(4) yes N6 C1 1.471(4) yes N6 C5 1.475(6) yes N6 C7 1.471(4) yes N10 C1 1.434(4) yes N10 C9 1.459(5) yes N10 C11 1.410(4) yes N22 C21 1.438(4) yes N22 C23 1.453(5) yes N22 C39 1.405(4) yes N26 C21 1.465(4) yes N26 C25 1.471(4) yes N26 C27 1.468(6) yes N30 C21 1.444(4) yes N30 C29 1.474(4) yes N30 C31 1.402(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139054375